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Oxidation of alkylarene C-H Bonds by tert-butyl hydroperoxide in the presence of cobalt, chromium, and vanadium acetylacetonates

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Abstract

Cobalt, chromium, and vanadium acetylacetonates catalyze efficient hydroperoxide oxidation of alkylarenes under mild conditions (20°C). The process takes place with either conservation, or destruction of carbon backbone of the hydrocarbon. Oxidizing agents are oxygen generated in the system, as well as tert-butylperoxy radicals. In the formation of end products alkylperoxy radicals originating in the substrates, tert-butylperoxy radicals, as well as metal-containing peroxides are involved. For the oxidative degradation processes a recombination reaction of the alkylperoxy radicals is suggested with the intermediate formation of 1,2-dioxetanes.

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References

  1. Sheldon, R.A. and van Doorn, J.A., J. Catal., 1973, vol. 31, no. 3, p. 427.

    Article  CAS  Google Scholar 

  2. Johnson, N.A. and Gould, E.S., J. Am. Chem. Soc., 1973, vol. 95, no. 8, p. 5198.

    Article  CAS  Google Scholar 

  3. Stepovik, L.P. and Gulenova, M.V., Zh. Obshch. Khim., 2009, vol. 79, no. 8, p. 1304.

    Google Scholar 

  4. Stepovik, L.P., Potkina, A.Yu., and Poddel’skii, A.I., Zh. Obshch. Khim., 2012, vol. 82, no. 9, p. 1473.

    Google Scholar 

  5. Muzart, J., Chem. Rev., 1992, vol. 92, no. 1, p. 113.

    Article  CAS  Google Scholar 

  6. Kaneda, K., Kawanishi, Y., Jitsukawa, K., and Teranishi, S., Tetrahedron Lett., 1983, vol. 24, no. 45, p. 5009.

    Article  CAS  Google Scholar 

  7. Itoh, T., Jitsukawa, K., Kaneda, K., and Teranishi, S., J. Am. Chem. Soc., 1979, vol. 101, no. 1, p. 159.

    Article  CAS  Google Scholar 

  8. Adam, W., Braun, E., Griesbeck, A., Luccini, V., Staab, E., and Will, B., J. Am. Chem. Soc., 1989, vol. 111, no. 1, p. 203.

    Article  Google Scholar 

  9. Glushakova, V.N., Skorodumova, N.A., Gryzina, O.Yu., and Razuvaev, G.A., Izv. Akad. Nauk, Ser. Khim., 1983, no. 5, p. 1193.

    Google Scholar 

  10. Adam, W., Haira, S., Herderich, M., and Saha-Möller, C.R., Org. Lett., 2000, vol. 2, no. 18, p. 2773.

    Article  CAS  Google Scholar 

  11. Pokucca, A.P., Le Bra, Zh., Myuzar Zh., Izv. Akad. Nauk, Ser. Khim., 2005, no. 2, p. 307.

    Google Scholar 

  12. Matienko, L.I., Skibida, I.P., and Maizus, Z.K., Izv. Akad. Nauk, Ser. Khim., 1975, no. 6, p. 1322.

    Google Scholar 

  13. Stepovik, L.P., Martynova, I.M., Dodonov, V.A., and Cherkasov, V.K., Izv. Akad. Nauk, Ser. Khim., 2002, no. 4, p. 590.

    Google Scholar 

  14. Stepovik, L.P., Gulenova, M.V., Martynova, I.M., Mar’yasin, B.A., and Cherkasov, V.K., Zh. Obshch. Khim., 2008, vol. 78, no. 2, p. 288.

    Google Scholar 

  15. Stepovik, L.P., Gulenova, M.V., Tishkina, A.N., and Cherkasov, V.K., Zh. Obshch. Khim., 2007, vol. 77, no. 7, p. 1173.

    Google Scholar 

  16. Russell, G.A., J. Am. Chem. Soc., 1957, vol. 79, no. 14, p. 3871.

    Article  CAS  Google Scholar 

  17. Hermans, I., Peeters, J., and Yacobs, P.A., J. Org. Chem., 2007, vol. 72, no. 8, p. 3057.

    Article  CAS  Google Scholar 

  18. Traylor, T.G., Russell, C.A., J. Am. Chem. Soc., 1965, vol. 87, no. 16, p. 3698.

    Article  CAS  Google Scholar 

  19. Timergazin, K.K. and Khursan, S.L., Izv. Akad. Nauk, Ser. Khim., 1996, no. 12, p. 2858.

    Google Scholar 

  20. Pritskov, V.V. and Suprun, V.Ya., Usp. Khim., 1996, vol. 65, no. 6, p. 538.

    Google Scholar 

  21. Stepovik, L.P., Gulenova, M.V., and Martynova, I.M., Zh. Obshch. Khim., 2005, vol. 75, no. 4, p. 545.

    Google Scholar 

  22. Mimoun, H., Saussine, L., Daire, E., Postel, M., Fisher, J., and Weiss, R., J. Am. Chem. Soc., 1983, vol. 105, no. 10, p. 3101.

    Article  CAS  Google Scholar 

  23. Stepovik, L.P., Gulenova, M.V., Kalacheva, I.A., and Potkina, A.Yu., Zh. Obshch. Khim., 2011, vol. 81, no. 3, p. 454.

    Google Scholar 

  24. Kolkhaun, H.M., Kholton, D., Tompson, D., and Tvigg, P., Novye puti organicheskogo sinteza. Prakticheskoe ispol’zovanie perekhodnyh metallov (New Ways of Organic Synthesis. The Practical Use of Transition Metals), Moscow: Khimiya, 1989, p. 365.

    Google Scholar 

  25. Korneev, N.N., Popov, A.F., and Krentsel’, B.A., Kompleksnye metallorganicheskie katalizatory (Complex Organometallic Catalysts), Leningrad: Khimiya, 1969, p. 84.

    Google Scholar 

  26. Brauer, G., Rukovodstvo po neorganicheskomu sintezu (A Guide to Inorganic Synthesis), Moscow: Mir, 1986, vol. 5, p. 1622.

    Google Scholar 

  27. Bartlett, P.D., Benzing, E.P., and Pincock, R.E., J. Am. Chem. Soc., 1960, vol. 82, no. 7, p. 1762.

    Article  CAS  Google Scholar 

  28. Slovar’ organicheskikh soedinenii (Dictionary of Organic Compounds), Moscow: Inostrannaya Literatura, 1949, vol. 1.

  29. Preparativnaya organicheskaya khimiya (Preparative Organic Chemistry), Moscow: Goshimizdat, 1959, p. 647.

  30. Davies, A.G., Organic Peroxides, London: Butterworths, 1961, p. 17.

    Google Scholar 

  31. Kornblum, N. and DeLaMare, H.E., J. Am. Chem. Soc., 1952, vol. 74, no. 12, p. 3079.

    Article  CAS  Google Scholar 

  32. Davies, A.G., Foster, R.V., and White, A.M., J. Chem. Soc., 1954, no. 7, p. 2200.

    Google Scholar 

  33. Huang, R.L. and Kum-Tatt, L., J. Chem. Soc., 1954, no. 7, p. 2570.

    Google Scholar 

  34. Polyanskii, N.G. and Safronenko, E.D., Zh. Prikl. Khim., 1961, vol. 34, no. 6, p. 1376.

    CAS  Google Scholar 

  35. Baujer, K., Analiz organicheskih soedinenii (Analysis of Organic Compounds), Moscow: Inostrannaya Literatura, 1953, p. 234.

    Google Scholar 

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Authors and Affiliations

  1. Lobachevskii Nizhny Novgorod State University, Gagarin av. 23, Nizhny Novgorod, 603950, Russia

    L. P. Stepovik & A. Yu. Potkina

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  1. L. P. Stepovik
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  2. A. Yu. Potkina
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Correspondence to L. P. Stepovik.

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Original Russian Text © L.P. Stepovik, A.Yu. Potkina, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 6, pp. 916–928.

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Stepovik, L.P., Potkina, A.Y. Oxidation of alkylarene C-H Bonds by tert-butyl hydroperoxide in the presence of cobalt, chromium, and vanadium acetylacetonates. Russ J Gen Chem 83, 1047–1059 (2013). https://doi.org/10.1134/S1070363213060078

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  • DOI: https://doi.org/10.1134/S1070363213060078

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